KR101571589B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound having excellent hole injecting and transporting ability and light emitting ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by incorporating the compound into one or more organic layers.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device including the organic compound, and more particularly to a novel organic compound having excellent hole injection ability, An organic electroluminescent device having improved characteristics such as efficiency, driving voltage, and lifetime.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to produce a high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce a characteristic organic material layer in the device, and it has led to the development of specialized materials used therefor.

When a voltage is applied between the two electrodes of the organic EL device, holes are injected into the organic layer and holes are injected into the organic layer, respectively. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron transporting layer material, and an electron injecting layer material depending on its function.

The material ('light emitting layer material') forming the light emitting layer of the organic EL device may be classified into blue, green and red light emitting layer materials depending on the light emitting color. In addition, yellow and orange light emitting layer materials are also used as light emitting layer materials for realizing better natural colors. In addition, a host / dopant system can be used as the light emitting layer material in order to increase the luminous efficiency through increase of color purity and energy transfer. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of a phosphorescent material can theoretically improve luminescence efficiency up to four times that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

NPB, BCP, Alq ₃ and the like represented by the following chemical formulas are widely known as the hole transporting layer material, the hole blocking layer material and the electron transporting layer material, and anthracene derivatives as a light emitting layer material are reported as fluorescent dopant / host material. In particular, there are metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , And is used as a material for a tread. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional luminescent layer materials have good luminescence characteristics, but have low glass transition temperature and are not very good in thermal stability, which is not satisfactory in terms of lifetime in an organic EL device. Therefore, development of a luminescent material having excellent performance is required.

Korea public patent 2011-0095482

In order to solve the above-described problems, it is an object of the present invention to provide a novel organic compound which can be used as a light emitting layer material and can improve the efficiency, lifetime and stability of a device when used in a light emitting layer of an organic electroluminescent device.

It is another object of the present invention to provide an organic electroluminescent device comprising the novel organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1)

In Formula 1,

Ring A is a 6-membered heterocycle containing CR ₃ and N, a 6-membered ring substituted with R ₃ , or a 6-membered heterocycle containing 2 N;

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) ₁ and X < ₂ > is N (Ar &_lt; ₁ >);

Y ₁ to Y ₄ are the same or different and each independently N or CR ₄ , and when CR ₄ is plural, they are the same or different from each other;

Provided that _{one of} R ₁ to R ₄ and Ar ₁ to Ar ₅ is a substituent represented by the following general formula (2)

In Formula 2,

a is 1 or 2;

L is a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 60 hetero arylene group, a substituted or unsubstituted aryl-tri-yl (aryl-triyl), or a substituted or Unsubstituted heteroaryl-triyl, < RTI ID = 0.0 >

However, when a is 1, L is a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group, or a substituted or unsubstituted 5 to 60 nuclear atoms of the heteroaryl group of,

when a is 2, L is a substituted or unsubstituted aryl-triyl, or a substituted or unsubstituted heteroaryl-triyl;

B is a substituted or unsubstituted carbazole group, or a substituent represented by the following general formula (3): wherein when B is plural, they are the same or different from each other;

In Formula 3,

Ring C is a 6-membered heterocycle containing CR ₇ and N, a 6-membered ring substituted by R ₇ , or a 6-membered heterocycle containing 2 N;

X ₃ and X ₄ is selected from the group consisting of each independently O, S, Se, N ( Ar 6), C (Ar 7) (Ar 8) and _{Si (Ar 9) (Ar 10} ),

Y ₅ to Y ₈ , equal to or different from each other, are each independently N or CR _8, wherein when CR _{8 is a} diradical, they are the same or different from each other;

Wherein one of R ₅ to R ₈ and Ar ₆ to Ar ₁₀ is a single bond and is connected to L of Formula 2;

R ₁ to R ₈ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ Substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, hwandoen C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted C ₁ ~ alkyloxy, substituted or unsubstituted of C ₄₀ unsubstituted heteroaryl group, substituted in the number of nuclear atoms of 5 to 60 ring or unsubstituted C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₃ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl silyl group, a substituted or unsubstituted C alkyl boron of ₁ ~ C ₄₀ A substituted or unsubstituted C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, a substituted or unsubstituted A C ₆ to C ₆₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, or form a condensed ring with or adjacent to an adjacent group;

Ar ₁ to Ar ₁₀ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ a cycloalkyl group, a substituted or unsubstituted number of 3 to 40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 60 of the hetero-substituted nucleus atoms an aryl group, A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl silyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C group ₆₀ aryl boron, substituted or unsubstituted C ₆ ~ C ₆₀ ring an aryl phosphine group, a substituted or unsubstituted C ₆ ~ C aryl phosphine oxide groups of _60, and a substituted or unsubstituted C ₆ ~ C ₆₀ aryl the It is selected from the group consisting of Min - gi;

The L arylene group, the heteroarylene group, the aryl-triyl, the heteroaryl-triyl; A carbazole group of B; Wherein R ₁ to R _8, and Ar ₁ to Ar ₁₀ alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boronic group, The substituents each independently introduced into the arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are independently selected from the group consisting of deuterium, halogen, cyano, nitro, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ An aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ If an aryl phosphine group, is selected from the group consisting of an aryl phosphine oxide of a C ₆ ~ C _60, a plurality of just the above substituent, all of which are identical to each other Or it may be different.

Also, the present invention is an organic EL device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the above formula And an organic EL device.

Herein, the organic compound layer including the compound represented by Formula 1 is selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, and is preferably a light emitting layer. When the compound represented by Formula 1 is included in the light emitting layer, it may be used as a host material and / or a dopant.

The compound represented by the formula (1) according to the present invention is excellent in heat resistance, hole injecting ability, hole transporting ability, and light emitting ability, and therefore can be applied to an organic material layer of an organic electroluminescent device, preferably a light emitting layer.

Accordingly, when the organic electroluminescent device includes the compound represented by Formula 1 as a hole injection layer material, a hole transport layer material, or a light emitting layer material (phosphorescent / fluorescent host, dopant) Life, efficiency (luminous efficiency, power efficiency), and the like can be greatly improved, and therefore, it can be effectively applied to a full color display panel and the like.

Hereinafter, the present invention will be described in detail.

The novel organic compound according to the present invention is a compound having an indoleindole-based basic skeleton in which an indole-base moiety and an indole-based moiety are fused, Or a structure in which an indole-based moiety is bonded to an indole-based moiety in which an indole-based moiety and a indole-based moiety are condensed. The compound represented by the formula (1) has a higher molecular weight than conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], has a high glass transition temperature, The hole injecting ability, the hole transporting ability, and the light emitting ability are excellent. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

The compound represented by the general formula (1) can be produced by reacting an indole-based moiety and an indole-based moiety in which an indole-based moiety is condensed with an indole-based moiety or a carbazole moiety And has a wide band gap (sky blue to red). Particularly, indole indole based moieties or carbazole groups are bonded to the N position of the indole based moiety among the basic skeletons condensed with the indole based moiety and the indole based moiety through a linking group (e.g., arylene, heteroarylene, etc.) The bandgap of the compound is widened and the triplet energy level is widened, thereby improving the phosphorescence characteristics of the device and improving the electron and / or hole transporting ability, luminous efficiency, driving voltage, lifetime characteristics, and the like. In addition, the electron transport ability and the like can be improved according to the type of the substituent introduced into the indole indole based basic skeleton. Accordingly, the compound of Formula 1 can be used as an organic material layer of an organic electroluminescent device, preferably a hole transporting layer material, a hole injecting layer material, a light emitting layer material, and preferably a light emitting layer material. The compound of formula (1) can also be used as a material for the electron transport layer by selectively introducing appropriate substituents. In particular, the compound of formula (1) can exhibit excellent characteristics as a light emitting layer material, particularly a host material, compared to conventional CBP due to the indole indole based basic skeleton.

In addition, the compounds represented by the above formula (1) have various aryl groups and / or heteroaryl groups introduced into the indole-indole-based basic skeleton to significantly increase the molecular weight of the compounds, thereby improving the glass transition temperature. It can have high thermal stability. Therefore, the device including the compound represented by the formula (1) of the present invention can greatly improve durability and lifetime characteristics.

In addition, the compound represented by the above formula (1) has a small difference in the triplet energy level and the singlet energy level, and the reverse energy transfer from triplet to singlet can occur. As a result, thermally activated delayed fluorescence occurs and the external quantum efficiency of the device is improved. Therefore, when the compound is used as a light emitting layer material, the luminous efficiency of the device can be increased.

When the compound of the present invention is used as a positive hole injection / transport layer, a blue, green and / or red phosphorescent host material or a fluorescent dopant material of an organic EL device, it is possible to exert an excellent effect in terms of efficiency and life have. Therefore, the compound according to the present invention can contribute greatly to improvement of the performance and lifetime of the organic EL device.

In the compound represented by formula (1) according to the present invention, ring A is a heterocyclic ring of a 6-membered ring containing CR ₃ and N, a 6-membered ring substituted by R ₃ , Is a 6-membered heterocycle containing N, preferably a 6-membered ring substituted with R < _{3 &} gt ;.

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) ₁ and X < ₂ > is N (Ar &_lt; ₁ >). Preferably, X ₁ and X ₂ are both N (Ar ₁ ), or X ₁ and X ₂ are each independently N (Ar ₁ ) or S.

Y ₁ to Y ₄ are the same or different and are each independently N or CR ₄ , and preferably Y ₁ to Y ₄ are all CR ₄ . Here, when a plurality of CR < ₄ > s are present, they are different from each other or the same.

Provided that _{one of} R ₁ to R ₄ and Ar ₁ to Ar ₅ is a substituent represented by the above formula (2).

In Formula 2, a is 1 or 2.

In addition, the L is a substituted or a C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted be 5 to 60 heteroaryl group of the ring nucleus atoms, a substituted or unsubstituted aryl unsubstituted -trimethyl- group (aryl-triyl group) , Or a substituted or unsubstituted heteroaryl-triyl group, provided that when a is 1, L is a substituted or unsubstituted C ₆ -C ₆₀ arylene group, or a substituted or unsubstituted nucleus And when a is 2, L is a substituted or unsubstituted aryl-triyl or a substituted or unsubstituted heteroaryl-triyl, or a substituted or unsubstituted heteroaryl- to be. Here, the aryl-triyl group is a trivalent aryl group, and the heteroaryl-triyl group is a trivalent heteroaryl group.

Aryl group, a heteroaryl group of the L, aryl-trimethyl group, aryl-trimethyl group, heteroaryl- one or more substituents each introduced into the tri-group are each independently selected from deuterium, halogen, cyano, nitro, C ₁ ~ C ₄₀ A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₂ to C ₄₀ alkyl And a boron group, provided that when a plurality of said substituents are plural, they may be the same or different from each other.

Preferably L is a bivalent or trivalent phenyl, biphenyl, naphthyl, indene, fluorenyl, carbazolyl, pyridine, pyrimidine, pyridazine, pyrazine, triazine, triazole, Halogen, cyano, nitro, a C ₁ to C ₄₀ alkyl group, a cycloalkyl group, a cycloalkyl group, a cycloalkyl group, a cycloalkyl group, a cycloalkyl group, , A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₂ to C ₄₀ alkylboron group Lt; / RTI > may be substituted with one or more substituents selected from the group consisting of

More preferably, L may be selected from the group consisting of substituents C1 to C76 described below, but is not limited thereto.

In the general formula (2), B is a substituted or unsubstituted carbazole group or a substituent represented by the general formula (3). At this time, when a plurality of B is present, they are different from each other or the same.

In Formula 3, Ring C is a six-membered heterocycle containing a CR ₇ and N, a 6-membered ring substituted with R ₇ , or a 6-membered ring containing 2 N And is preferably a 6-membered ring substituted by R < _{7 &} gt ;.

In addition, the X ₃ and X ₄ is selected from the group consisting of each independently O, S, Se, N ( Ar 6), C (Ar 7) (Ar 8) and _{Si (Ar 9) (Ar 10} ), Wherein at least one of X ₃ and X ₄ is N (Ar ₆ ). Preferably, X ₃ and X ₄ are both N (Ar ₆ ), or X ₃ and X ₄ are each independently N (Ar ₆ ) or S.

Y ₅ to Y ₈ are the same or different and each independently N or CR ₈ , and preferably Y ₅ to Y ₈ are all CR ₈ . At this time, when a plurality of CR _{8 s} are present, they are different from each other or the same.

Provided that one of R ₅ to R ₈ and Ar ₅ to Ar ₈ is a single bond and is connected to L of formula (2).

R ₁ to R ₈ are each independently hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 ring atoms, a C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₃ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group , A substituted or unsubstituted C ₆ to C ₆₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group Can be selected. However, considering a wide band-gap and thermal stability, R ₁ to R ₈ are each independently hydrogen, a C ₆ to C ₆₀ aryl group (e.g., phenyl, naphthyl, biphenyl) (For example, pyridine).

In this case, the alkyl group of the R ₁ to R _8, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl The substituent groups introduced into the phosphine group, the arylphosphine oxide group and the arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ aryloxy group, C _A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, and And an arylphosphine oxide group having ₆ to ₆₀ carbon atoms, provided that when they are plural substituents, they may be the same or different from each other .

Ar ₁ to Ar ₁₀ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nuclear atoms of 3 to 40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted number of 5 to 60 heteroaryl unsubstituted nucleus atoms an aryl group , A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a C ₆ ~ C aryl silyl group of _60, a substituted or unsubstituted C ₁ ~ C ₄₀ group of an alkyl boron, substituted or unsubstituted C ₆ ~ C group ₆₀ aryl boron, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₆₀ aryl ah Groups may be selected from the group consisting of.

Preferably, Ar ₁ to Ar ₁₀ are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nucleus atoms.

Alkyl group of said Ar ₁ to Ar _10, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group , Arylphosphine oxide group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₆₀ heteroaryl group, C ₄₀ alkylsilyl group, a group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, and C ₆ ~ C ₆₀ aryl phosphine oxide is selected from the group consisting of pins, not just when the plurality of the replacement unit, all of which are the same or can be different from each other have.

In the compound according to the present invention, each of R ₁ to R ₈ , and Ar ₁ to Ar ₁₀ may be independently selected from the group consisting of hydrogen, substituent groups S1 to S177 shown below, but is not limited thereto. Provided that at least one of R ₁ to R ₄ and Ar ₁ to Ar ₅ is a substituent represented by the above general formula (2), and one of R ₅ to R ₈ and Ar ₆ to Ar ₁₀ is a single bond, L.

In the compound according to the present invention, the substituent represented by the formula (3) may be selected from the substituents represented by the following formulas (3a) to (3f), but is not limited thereto.

[Chemical Formula 3]

;

;

(3b)

;

;

[Chemical Formula 3c]

;

;

(3d)

;

;

[Formula 3e]

;

;

(3f)

In the above formulas (3a) to (3f)

X ₃ and X ₄ are each independently selected from the group consisting of O, S, Se, N (Ar ₆ ), C (Ar ₇ ) (Ar ₈ ), and Si (Ar ₉ ) (Ar ₁₀ );

Provided that one of R ₅ to R ₈ and Ar ₆ to Ar ₁₀ is a single bond and is connected to L of Formula 2;

R ₅ to R ₈ and Ar ₆ to Ar ₁₀ are each as defined in formula (1)

Here, the plural R < ₇ > s are the same as or different from each other, and a plurality of R < ₈ >

Examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formulas (4) to (9), but are not limited thereto.

In the above formulas 4 to 9,

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) ₁ and X < ₂ > is N (Ar &_lt; ₁ >);

Provided that _{one of} R ₁ to R ₄ , and Ar ₁ to Ar ₅ is a substituent represented by the above formula (2);

R ₁ to R ₄ , and Ar ₁ to Ar ₅ are each as defined in formula (1).

Examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formula (10), but the present invention is not limited thereto.

In Formula 10,

X ₁ , Y ₁ to Y ₄ , ring A, R ₁ , R ₂ , L, a and B are each as defined in formula (1)

Here, the plurality of R < ₃ > s may be the same as or different from each other, and the plurality of R < ₄ >

Examples of the compound represented by the formula (1) include compounds represented by the following formulas (11) to (16), but are not limited thereto.

In the above Formulas 11 to 16,

X ₁ , R ₁ to R ₄ , L, a and B are each as defined in formula (1)

Here, the plurality of R < ₃ > s may be the same as or different from each other, and the plurality of R < ₄ >

Examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formula (17), but the present invention is not limited thereto.

In Formula 17,

X ₁ , X ₃ , Y ₁ to Y ₈ , R ₁ , R ₂ , R ₅ , R ₆ , ring A, ring C, L and a are each as defined in formula (1).

Examples of the compound represented by the formula (1) include compounds represented by the following formulas (18) to (23), but are not limited thereto.

In the above formulas 18 to 23,

X ₁ , X ₃ , Y ₅ to Y ₈ , R ₁ to R ₆ , ring C, L and a are each as defined in formula (1)

Here, the plurality of R < ₃ > s may be the same as or different from each other, and the plurality of R < ₄ >

Specific examples of the compound represented by Formula 1 include compounds represented by the following formulas CH-1 to CH-281, but are not limited thereto.

The term "unsubstituted alkyl" used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec Butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "unsubstituted alkenyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. do. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "unsubstituted alkynyl" means a monovalent functional group obtained by removing a hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond do. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, "unsubstituted cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, "unsubstituted heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, wherein at least one of the rings Carbon, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.

In the present invention, "unsubstituted aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Two or more rings may be attached to each other in a pendant or fused form to each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, the "unsubstituted heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, , One to three carbons are replaced with a heteroatom such as N, O, S or Se. At this time, heteroaryl can be attached to two or more rings in a form of pendant or fused to each other, and further includes a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. Includes rings and is also meant to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

In the present invention, "unsubstituted alkyloxy" means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

In the present invention, "unsubstituted aryloxy" means a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "unsubstituted alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, and " Unsubstituted arylamine "means an amine substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "unsubstituted alkyl boron" means boron substituted with alkyl having 1 to 40 carbon atoms, and "unsubstituted aryl boron" means boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "unsubstituted arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "unsubstituted arylphosphine oxide" means a compound having 6 to 60 carbon atoms substituted with aryl Oxide.

Further, in the present invention, the term "fused ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compound represented by formula (1) according to the present invention can be synthesized according to a general synthesis method [ Chem. Rev. , ≪ / RTI > 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995)). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the above-mentioned formula (1) (preferably a compound represented by the formula (4-23)).

Specifically, the organic electroluminescent device according to the present invention includes an anode; A cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the organic material layers is formed of a compound represented by the formula (1) (preferably a compound represented by the formula (4-23)) And at least one of them.

The at least one organic material layer may include a hole injection layer, a hole transport layer, and a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the one or more organic layers including the compound of Formula 1 may be a hole transporting layer, a hole injecting layer, or a light emitting layer, more preferably a light emitting layer. When the compound of Formula 1 is included in the light emitting layer, the compound of Formula 1 may be used as a phosphorescent or fluorescent host material and / or a dopant. When the organic electroluminescent device includes the compound as described above, the luminous efficiency, brightness, power efficiency, thermal stability, and lifetime of the device can be improved.

The structure of the organic EL device according to the present invention is not particularly limited, and examples thereof include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and a cathode sequentially laminated. At this time, at least one of the hole injecting layer, the hole transporting layer and the light emitting layer may contain at least one compound represented by the above formula (1). An electron injection layer may be disposed on the electron transport layer.

In addition, the organic EL device according to the present invention may have an insulating layer or an adhesive layer inserted into the interface between the electrode and the organic layer as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

The organic electroluminescent device according to the present invention may be formed by using other materials and methods known in the art, except that one or more of the organic material layers include the compound represented by the above formula (1) .

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

As the substrate usable in the present invention, a silicon wafer, quartz or glass plate, a metal plate, a plastic film or a sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Preparation Example 1] Synthesis of Compound IC-1

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

(25 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3 Dioxaborolane (48.58 g, 0.191 mol), Pd (dppf) Cl ₂ (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4- And the mixture was stirred at 130 DEG C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: ethyl acetate (EA) = 10: 1 (v / v) 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22.32 g, yield 72%).

¹ H-NMR:? 1.24 (s, 12H), 6.45 (d, IH), 7.27 (d, IH), 7.42 s, 1 H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) -1H- indole Synthesis of

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -1H-indole ( 22 g, 90.49 mmol) to, NaOH (9.05 g, 226.24 mmol ) and _{THF / H 2 O (400 ml} / 200 ml) and mixed, and then, Pd (PPh ₃ at 40 ℃ ) ₄ (4.36 g, 5 mol%) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto, followed by filtration to obtain an organic layer. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1H-indole (11.32 g, yield 63%).

^{1 H-NMR: δ 6.47 (} d, 1H), 7.25 (d, 1H), 7.44 (d, 1H), 7.53 (d, 1H), 7.65 (t, 1H), 7.86 (t, 1H), 7.95 ( (s, 1 H), 8.00 (d, 1 H), 8.09 (t,

&Lt; Step 3 > 5- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

Iodobenzene (14.13 g, 69.26 mmol) and Cu powder (0.29 g, 4.62 mmol) obtained in Step 2 of Preparation Example 1 were added to a solution of 5- (2-nitrophenyl) mmol), K ₂ CO ₃ (6.38 g, 46.17 mmol), Na ₂ SO ₄ (6.56 g, 46.17 mmol), and nitrobenzene (200 ml), followed by stirring at 190 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1- 71%).

^{1 H-NMR: δ 6.48 (} d, 1H), 7.26 (d, 1H), 7.45 (m, 3H), 7.55 (m, 4H), 7.63 (t, 1H), 7.84 (t, 1H), 7.93 ( s, 1 H), 8.01 (d, 1 H), 8.11 (t, 1 H)

&Lt; Step 4 > IC -1 and IC Synthesis of -2

Phenyl-1H-indole (5 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1,2-dichlorobenzene (50 ml ) Were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and then extracted with dichloromethane. The obtained organic layer was washed with water and dried over MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain the compound IC-1 (2.38 g, yield 53% 1.30 g, yield: 29%).

Compound ¹ H-NMR of the IC-1: δ 6.99 (d , 1H), 7.12 (t, 1H), 7.27 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.50 (d, 1H), 7.60 (m, 5H), 7.85 (d, 1H), 8.02

Compound IC-2 ¹ of H-NMR: δ 6.98 (d , 1H), 7.13 (t, 1H), 7.26 (t, 1H), 7.33 (d, 1H), 7.42 (t, 1H), 7.51 (s, 1H), 7.61 (m, 5H), 7.84 (d,

[Preparation Example 2] Synthesis of compound IC-3 and IC-4

<Step 1> Synthesis of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

Preparation Example The same procedure as in <Step 1> of Preparation Example 1 was carried out except that 6-bromo-1H-indole (25 g, 0.128 mol) was used instead of 5-bromo-1H-indole used in <Step 1> Was performed to obtain 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole.

¹ H-NMR:? 1.25 (s, 12H), 6.52 (d, IH), 7.16 (d, IH), 7.21 s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl ) -1H- indole Synthesis of

Step 1 of Preparation Example 2 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole used in <Step 2> Except that the 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22 g, 90.49 mmol) (2-nitrophenyl) -1H-indole was obtained in the same manner as in < Step 2 >

^{1 H-NMR: δ 6.57 (} d, 1H), 7.07 (d, 1H), 7.24 (d, 1H), 7.35 (s, 1H), 7.43 (t, 1H), 7.50 (d, 1H), 7.58 ( t, 1 H), 7.66 (d, 1 H), 7.78 (d,

&Lt; Step 3 > 6- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

(2-nitrophenyl) -1H-indole (11 g, 46.17 g) obtained in Step 2 of Preparation Example 2 was used in place of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1-phenyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H-NMR: δ 6.81 (} d, 1H), 7.12 (t, 1H), 7.22 (t, 1H), 7.35 (s, 1H), 7.43 (d, 1H), 7.51 (m, 3H), 7.56 ( (m, 2H), 7.62 (m, 2H), 7.85 (d,

&Lt; Step 4 > IC -3 and IC Synthesis of -4

(2-nitrophenyl) -1-phenyl-1H-indole obtained in Step 3 of Preparation Example 3 was used instead of 5- (2-nitrophenyl) -indole (5 g, 15.91 mmol) in the same manner as in <Step 4> of Preparation Example 1, except that 1-indole (5 g, 15.91 mmol)

¹ of compound IC-3 H-NMR: δ 6.80 (d, 1H), 7.11 (t, 1H), 7.23 (t, 1H), 7.42 (d, 1H), 7.50 (m, 3H), 7.57 (m, 2H), 7.63 (m, 2H), 7.86 (d,

Compound IC-4 ¹ H-NMR of: δ 6.81 (d, 1H) , 7.12 (t, 1H), 7.22 (t, 1H), 7.43 (s, 1H), 7.51 (m, 3H), 7.58 (m, 2H), 7.64 (m, 2H), 7.85 (s, 1H), 8.02

[Preparation Example 3] Synthesis of Compound IC-5

<Step 1> Synthesis of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

Step 1> of Preparation Example 1 was repeated except that 4-bromo-1H-indole (25 g, 0.128 mol) was used instead of 5-bromo-1H-indole used in <Step 1> The same procedure was followed to obtain 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole.

^{1 H NMR: δ 1.26 (s} , 12H), 6.43 (d, 1H), 7.26 (t, 1H), 7.48 (d, 1H), 7.74 (d, 1H), 7.85 (d, 1H), 8.23 (s , 1H)

<Step 2> Synthesis of 4- (2- nitrophenyl ) -1H- indole Synthesis of

Step 1 of Preparation Example 3 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole used in Step 2 of Preparation Example 1, -1,4-dioxaborolan-2-yl) -1H-indole (22 g, 90.49 mmol) obtained in Preparation Example 1 was used instead of 4- (4,4,5,5-tetramethyl- The same procedure as in <Step 2> was conducted to obtain 4- (2-nitrophenyl) -1H-indole.

^{1 H NMR: δ 6.45 (d} , 1H), 7.27 (t, 1H), 7.50 (d, 1H), 7.66 (t, 1H), 7.75 (d, 1H), 7.89 (m, 2H), 7.99 (d , &Lt; / RTI &gt; 1H), 8.04 (d, 1H), 8.24

<Step 3> Synthesis of 4- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

(2-nitrophenyl) -1H-indole (11 g, 46.17 g) obtained in Step 2 of Preparation Example 3 was used instead of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1-phenyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H NMR: δ 6.47 (d} , 1H), 7.28 (t, 1H), 7.47 (m, 2H), 7.52 (m, 2H), 7.60 (m, 2H), 7.67 (t, 1H), 7.75 (d , 7.89 (m, 2H), 8.00 (d, IH), 8.06 (d, IH)

&Lt; Step 4 > IC Synthesis of -5

(2-nitrophenyl) -1-phenyl-1H-indole obtained in Step 3 of Preparation Example 3 was used instead of 5- (2-nitrophenyl) 1H-indole (5 g, 15.91 mmol) in the same manner as in <Step 4> of Preparation Example 1 to give compound IC-5.

^{1 H NMR: δ 6.49 (d} , 1H), 7.29 (t, 1H), 7.46 (m, 2H), 7.54 (m, 2H), 7.61 (d, 1H), 7.69 (t, 1H), 7.74 (d , 8.01 (d, IH), 8.04 (d, IH), 8.23 (s, IH)

[Preparation Example 4] Synthesis of IC-6

<Step 1> Synthesis of 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

Except that 7-bromo-1H-indole (25 g, 0.128 mol) was used instead of 5-bromo-1H-indole used in <Step 1> of Preparation Example 1, The same procedure was followed to obtain 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole.

^{1 H NMR: δ 1.25 (s} , 12H), 6.43 (d, 1H), 7.25 (d, 1H), 7.45 (t, 1H), 7.56 (d, 1H), 7.71 (d, 1H), 8.22 (s , 1H)

&Lt; Step 2 > 7- (2- nitrophenyl ) -1H- indole Synthesis of

Step 1 of Preparation Example 4 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole used in <Step 2> -Indole (22 g, 90.49 mmol) obtained in Preparation Example 1 was used instead of 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (2-nitrophenyl) -1H-indole was obtained by following the same procedure as in Step 2).

^{1 H NMR: δ 6.42 (d} , 1H), 7.24 (d, 1H), 7.43 (t, 1H), 7.55 (d, 1H), 7.70 (m, 2H), 7.88 (t, 1H), 8.01 (d , 8.11 (d, 1 H), 8.23 (s, 1 H)

&Lt; Step 3 > 7- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

(2-nitrophenyl) -1H-indole (11 g, 46.17 g) obtained in Step 2 of Preparation Example 4 was used in place of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1-phenyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H NMR: δ 6.43 (d} , 1H), 7.26 (d, 1H), 7.44 (m, 3H), 7.56 (m, 4H), 7.71 (m, 2H), 7.89 (t, 1H), 8.02 (d , &Lt; / RTI &gt; 1H), 8.10 (d, 1H)

&Lt; Step 4 > IC Synthesis of -6

(2-nitrophenyl) -1-phenyl-1H-indole obtained in Step 3 of Preparation Example 4 was used instead of 5- (2-nitrophenyl) 1H-indole (5 g, 15.91 mmol) in the same manner as in <Step 4> of Preparation Example 1 to obtain a compound IC-6.

^{1 H NMR: δ 6.45 (d} , 1H), 7.24 (d, 1H), 7.45 (m, 3H), 7.57 (m, 3H), 7.63 (d, 1H), 7.70 (d, 1H), 7.88 (t , 8.00 (d, IH), 8.09 (d, IH), 8.22 (s, IH)

[Preparation Example 5] Synthesis of compound IC-7

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole was synthesized in the same manner as in <Step 1> of Preparation Example 1.

&Lt; Step 2 > 5- (5- bromo -2- nitrophenyl ) -1H- indole Synthesis of

Step 2 of Preparation Example 1 was repeated except that 2,4-dibromo-1-nitrobenzene (21.04 g, 75.41 mmol) was used instead of 1-bromo-2-nitrobenzene used in Step 2 of Preparation Example 1 (5-bromo-2-nitrophenyl) -1H-indole was obtained.

^{1 H NMR: δ 6.45 (d} , 1H), 7.26 (d, 1H), 7.45 (d, 1H), 7.55 (d, 1H), 7.64 (d, 1H), 7.85 (d, 1H), 7.96 (s , &Lt; / RTI &gt; 1H), 8.13 (s, 1H), 8.21

&Lt; Step 3 > 5- (5- bromo -2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

(5-bromo-2-nitrophenyl) -1H-indole obtained in Step 2 of Preparation Example 5 instead of 5- (2-nitrophenyl) -1H-indole used in Step 3 of Preparation Example 1 (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1, except that the compound (14.59 g, 46.17 mmol)

^{1 H NMR: δ 6.44 (d} , 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 4H), 7.65 (d, 1H), 7.86 (d, 1H), 7.95 (s , &Lt; / RTI &gt; 1H), 8.11 (s, 1H)

&Lt; Step 4 > IC Synthesis of -7

(5-bromo-2-nitrophenyl) -1-phenyl-1H-indole obtained in Step 3 of Preparation Example 5 was used instead of 5- (2-nitrophenyl) 1-phenyl-1H-indole (6.24 g, 15.91 mmol) The procedure of <Step 4> of Preparation Example 1 was repeated to obtain a compound IC-7.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.26 (d, 1H), 7.38 (m, 2H), 7.45 (d, 1H), 7.51 (d, 1H), 7.57 (m, 3H), 7.64 ( (d, IH), 7.85 (d, IH), 8.10 (s, IH), 8.23

[Preparation Example 6] Synthesis of Compound IC-8

<Step 1> 6- (5- bromo -2- nitrophenyl ) -1H- indole Synthesis of

2,4-dibromo-1-nitrobenzene (21.11 g, 75.41 mmol) was used instead of 1-bromo-2-nitrobenzene used in Step 2 of Preparation Example 1 and 5- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22 (5-bromo-2-nitrophenyl) -1H-indole was obtained by following the procedure of <Step 2> of Preparation Example 1,

^{1 H NMR: δ 6.51 (d} , 1H), 7.31 (d, 1H), 7.50 (d, 1H), 7.60 (d, 1H), 7.69 (d, 1H), 7.90 (d, 1H), 8.01 (s , &Lt; / RTI &gt; 1H), 8.14 (s, 1H), 8.25

&Lt; Step 2 > 6- (5- bromo -2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

(5-bromo-2-nitrophenyl) -1H-indole (obtained in Step 1 of Preparation Example 6 instead of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 6-bromo-2-nitrophenyl) -1-phenyl-1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1 except that the compound (14.59 g, 46.17 mmol)

^{1 H NMR: δ 6.49 (d} , 1H), 7.30 (d, 1H), 7.51 (m, 3H), 7.61 (m, 4H), 7.70 (d, 1H), 7.91 (d, 1H), 8.00 (s , &Lt; / RTI &gt; 1H), 8.16 (s, 1H)

&Lt; Step 3 > IC Synthesis of -8

(5-bromo-2-nitrophenyl) -1-phenyl-1H-indole obtained in Step 2 of Preparation Example 6 was used instead of 5- (2-nitrophenyl) 1-phenyl-1H-indole (6.23 g, 15.91 mmol) was used in place of the compound obtained in Step 4 of Preparation Example 1 to obtain the compound IC-8.

^{1 H-NMR: δ 6.47 (} d, 1H), 7.28 (d, 1H), 7.40 (m, 2H), 7.47 (d, 1H), 7.53 (d, 1H), 7.59 (m, 3H), 7.66 ( (d, IH), 7.87 (d, IH), 8.12 (s, IH), 8.25

[Preparation Example 7] Synthesis of compound IC-9

<Step 1> 5- (2- nitrophenyl ) -1-o- tolyl -1H- indole Synthesis of

The same procedure as in <Step 3> of Preparation Example 1 was carried out except that 1-bromo-2-methylbenzene (11.77 g, 69.26 mmol) was used instead of the iodobenzene used in <Step 3> - (2-nitrophenyl) -1-o-tolyl-1H-indole.

^{1 H-NMR: δ 1.92 (} s, 3H), 6.47 (d, 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 3H), 7.64 (t, 1H), 7.85 ( t, 1 H), 7.94 (s, 1 H), 8.00 (d,

&Lt; Step 2 > IC - 9 of  synthesis

(2-nitrophenyl) -1-o-indole obtained in Step 1 of Preparation Example 7 was used instead of 5- (2-nitrophenyl) -1- The same procedure as in <Step 4> of Preparation Example 1 was carried out except that tolyl-1H-indole (5.22 g, 15.91 mmol) was used to obtain compound IC-9.

^{1 H-NMR: δ 1.93 (} s, 3H), 6.98 (d, 1H), 7.11 (t, 1H), 7.28 (t, 1H), 7.31 (d, 1H), 7.42 (t, 1H), 7.51 ( (d, IH), 7.61 (m, 4H), 7.86 (d,

[Preparation Example 8] Synthesis of Compound IC-10

<Step 1> 1- ( biphenyl -4- yl ) -5- (2- nitrophenyl ) -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 4-bromobiphenyl (16.07 g, 69.26 mmol) was used instead of the iodobenzene used in Step 3 of Preparation Example 1 to prepare 1- (biphenyl- 4-yl) -5- (2-nitrophenyl) -1H-indole.

^{1 H-NMR: δ 6.73 (} d, 1H), 7.18 (d, 1H), 7.39 (m, 2H), 7.47 (m, 3H), 7.54 (d, 1H), 7.59 (m, 3H), 7.64 ( m, 4H), 7.75 (d, 2H), 7.82 (d, IH)

&Lt; Step 2 > IC Synthesis of -10

(Biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole obtained in Step 1 of Preparation Example 8 was used instead of 5- (2-nitrophenyl) The same procedure as in <Step 4> of Preparation Example 1 was conducted except that 2-nitrophenyl-1H-indole (6.20 g, 15.91 mmol) was used to obtain compound IC-10.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.20 (d, 1H), 7.42 (m, 2H), 7.51 (m, 3H), 7.56 (d, 1H), 7.62 (m, 3H), 7.68 ( (d, 2H), 7.85 (d, 1H), 10.45 (s, 1H)

[Preparation Example 9] Synthesis of compound IC-11

&Lt; Step 1 > IC Synthesis of -11-1

Step 3 of Preparation Example 1 was repeated except that 1-bromo-3,5-diphenyl benzene (21.33 g, 69.26 mmol) was used instead of the iodobenzene used in Step 3 of Preparation Example 1 To give compound IC-11-1.

^{1 H-NMR: δ 6.98 (} d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (t, 2H), 7.46 (m, 6H), 7.58 (d, 1H), 7.81 ( (d, IH), 7.87 (m, 4H), 7.93

&Lt; Step 2 > IC Synthesis of -11

The compound IC-11-1 (7.41 g, 15.91 mmol) obtained in Step 1 of Preparation Example 9 was used instead of 5- (2-nitrophenyl) -1-phenyl-1H- indole used in Step 4 of Preparation Example 1 ) Was used in place of Compound (I-2), the compound IC-11 was obtained in the same manner as in <Step 4> of Preparation Example 1.

^{1 H-NMR: δ 6.97 (} d, 1H), 7.10 (t, 1H), 7.23 (t, 1H), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, 1H), 7.80 ( (d, IH), 7.86 (d, IH), 7.86 (d,

[Preparation Example 10] Synthesis of Compound IC-12

<Step 1> Synthesis of 5- (2-nitrophenyl) -1- (2- (trifluoromethyl) phenyl) -1H-indole

The same procedure as in <Step 3> of Preparation Example 1 was carried out except that 1-bromo-2- (trifluoromethyl) benzene (15.58 g, 69.26 mmol) was used instead of the iodobenzene used in <Step 3> in Preparation Example 1 To obtain 5- (2-nitrophenyl) -1- (2- (trifluoromethyl) phenyl) -1H-indole.

¹ H-NMR:? 6.48 (d, IH), 7.26 (d, IH), 7.47 (m, 3H), 7.57 s, 1 H), 8.01 (d, 1 H), 8.13 (t, 1 H)

&Lt; Step 2 > IC Synthesis of -12

(2-nitrophenyl) -1- (2-nitrophenyl) -1H-indole obtained in Step 1 of Preparation Example 10 was used in place of 5- (2-nitrophenyl) (trifluoromethyl) phenyl) -1H-indole (6.23 g, 15.91 mmol) was used in place of the compound obtained in Step 4 of Preparation Example 1 to obtain the compound IC-12.

^{1 H-NMR: δ 6.97 (} d, 1H), 7.12 (t, 1H), 7.29 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.52 (d, 1H), 7.60 ( (s, 1H), 7.85 (d, 1H), 8.01 (d,

[Preparation Example 11] Synthesis of Compound IC-13

<Step 1> 1- ( biphenyl -3- yl ) -5- (2- nitrophenyl ) -1H- indole Synthesis of

The same procedure as in <Step 3> of Preparation Example 1 was carried out except that 3-bromobiphenyl (16.07 g, 69.26 mmol) was used instead of the iodobenzene used in <Step 3> of Preparation Example 1 to obtain 5- (2- nitrophenyl) -1- (2- (trifluoromethyl) phenyl) -1H-indole.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.19 (d, 1H), 7.38 (m, 2H), 7.48 (m, 3H), 7.52 (d, 1H), 7.58 (m, 3H), 7.65 ( m, 4H), 7.76 (m, 2H), 7.85 (d, IH)

&Lt; Step 2 > IC Synthesis of -13

(Biphenyl-3-yl) -5- (2-nitrophenyl) -1H-indole obtained in Step 1 of Preparation Example 11 was used instead of 5- (2-nitrophenyl) (IC-13) was obtained by following the procedure of <Step 4> of Preparation Example 1 except that 2-nitrophenyl-1H-indole (6.20 g, 15.91 mmol)

^{1 H-NMR: δ 6.74 (} d, 1H), 7.21 (d, 1H), 7.41 (m, 2H), 7.52 (m, 3H), 7.56 (d, 1H), 7.61 (m, 3H), 7.69 ( m, 3H), 7.77 (m, 2H), 7.86 (d,

[Preparation Example 12] Synthesis of compound IC-14

<Step 1> 1- ( biphenyl -3- yl ) -6- (2- nitrophenyl ) -1H- indole Synthesis of

Using 2-nitrophenyl-1H-indole and 3-bromobiphenyl (11 g, 46.17 mmol) instead of 5- (2-nitrophenyl) -1H-indole used in Step 3 of Preparation Example 1 and iodobenzene (Biphenyl-3-yl) -6- (2-nitrophenyl) -1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1 above.

^{1 H-NMR: δ 6.76 (} d, 1H), 7.18 (d, 1H), 7.37 (m, 2H), 7.47 (m, 3H), 7.51 (d, 1H), 7.57 (m, 3H), 7.64 ( m, 4H), 7.75 (m, 2H), 7.86 (d, IH)

&Lt; Step 2 > IC Synthesis of -14

(Biphenyl-3-yl) -6- (2-nitrophenyl) -1 H-indole obtained in Step 1 of Preparation Example 12 was used instead of 5- (2-nitrophenyl) Compound 4 was obtained in the same manner as in <Step 4> of Preparation Example 1 except that 2-nitrophenyl-1H-indole (6.20 g, 15.91 mmol) was used.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.20 (d, 1H), 7.40 (m, 2H), 7.51 (m, 3H), 7.57 (d, 1H), 7.62 (m, 3H), 7.70 ( (s, 3H), 7.76 (m, 2H), 7.85 (d,

[Preparation Example 13] Synthesis of compound IC-15

<Step 1> 1- ( biphenyl -4- yl ) -6- (2- nitrophenyl ) -1H- indole Synthesis of

Using 2-nitrophenyl-1H-indole and 4-bromobiphenyl (11 g, 46.17 mmol) instead of 5- (2-nitrophenyl) -1H-indole and iodobenzene used in Step 3 of Preparation Example 1 (Biphenyl-4-yl) -6- (2-nitrophenyl) -1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H-NMR: δ 6.74 (} d, 1H), 7.19 (d, 1H), 7.40 (m, 2H), 7.46 (m, 3H), 7.55 (d, 1H), 7.58 (m, 3H), 7.63 ( m, 4H), 7.75 (d, 2H), 7.83 (d, IH)

&Lt; Step 2 > IC Synthesis of -15

(Biphenyl-4-yl) -6- (2-nitrophenyl) -1H-indole obtained in Step 1 of Preparation Example 13 was used instead of 5- (2-nitrophenyl) 15 was obtained by following the procedure of <Step 4> of Preparation Example 1, except that 2-nitrophenyl-1H-indole (6.20 g, 15.91 mmol) was used.

^{1 H-NMR: δ 6.74 (} d, 1H), 7.19 (d, 1H), 7.43 (m, 2H), 7.52 (m, 3H), 7.57 (d, 1H), 7.63 (m, 3H), 7.69 ( (m, 3H), 7.75 (d, 2H), 7.86 (d,

[ Preparation Example  14] Compound IC Synthesis of -16

&Lt; Step 1 > IC Synthesis of -16-1

(2-nitrophenyl) -1H-indole (11 g, 46.17 mmol) was used instead of 5- (2-nitrophenyl) -1-phenyl-1H- indole used in Step 3 of Preparation Example 1, iodobenzene The same procedure as in <Step 3> of Preparation Example 1 was conducted except that 1-bromo-3,5-diphenyl benzene (14.13 g, 69.26 mmol) was used instead of 1-bromo-3,5-diphenyl benzene.

^{1 H-NMR: δ 6.98 (} d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (m, 2H), 7.45 (m, 6H), 7.57 (d, 1H), 7.80 ( (d, IH), 7.86 (m, 4H), 7.92

&Lt; Step 2 > IC Synthesis of -16

IC-16-1 (7.41 g, 15.91 mmol) obtained in Step 1 of Preparation Example 14 was used instead of 5- (2-nitrophenyl) -1-phenyl-1H- indole used in Step 4 of Preparation Example 1, , The same procedure as in <Step 4> of Preparation Example 1 was conducted to obtain a compound IC-16.

^{1 H-NMR: δ 6.97 (} d, 1H), 7.10 (t, 1H), 7.23 (t, 1H), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, 1H), 7.80 ( (d, IH), 7.86 (d, IH), 7.86 (m,

[Preparation Example 15] Synthesis of compound IC-17

<Step 1> Synthesis of 6- (2-nitrophenyl) -1- (3- (trifluoromethyl) phenyl) -1H-indole

(2-nitrophenyl) -1-phenyl-1H-indole used in Step 3 of Preparation Example 1 and 6- (2-nitrophenyl) -1H-indole and 1-bromo-3- (trifluoromethyl) (2-nitrophenyl) -1- (3- (trifluoromethyl) phenyl) -1H (4-fluorophenyl) -1H-benzimidazole was prepared by following the procedure of Step 3 of Preparation Example 1, -indole.

^{1 H-NMR: δ 6.80 (} d, 1H), 7.11 (t, 1H), 7.21 (t, 1H), 7.36 (s, 1H), 7.42 (s, 1H), 7.50 (m, 2H), 7.55 ( (m, 2H), 7.63 (m, 2H), 7.86 (d,

&Lt; Step 2 > IC Synthesis of -17

(2-nitrophenyl) -1- (3-nitrophenyl) -1 H-indole obtained in Step 1 of Preparation Example 15 was used in place of 5- (2-nitrophenyl) - (trifluoromethyl) phenyl) -1H-indole (6.07 g, 15.91 mmol) was used in place of the compound obtained in Step 4 of Preparation Example 1 to obtain compound IC-17.

^{1 H-NMR: δ 6.81 (} d, 1H), 7.12 (t, 1H), 7.24 (t, 1H), 7.43 (d, 1H), 7.51 (m, 2H), 7.58 (m, 2H), 7.64 ( (m, 2H), 7.85 (d, 1H), 8.02 (d,

[Preparation Example 16] Synthesis of compound IC-18

<Step 1> Synthesis of 3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9-phenyl-9H-carbazole

(2-nitrophenyl) -1H-indole (11 g, 46.17 mmol) and 3-bromo-9-indole were used in place of 5- (2-nitrophenyl) (5- (2-nitrophenyl) -1H-indol-1 (1) was obtained by following the same procedure as <Step 3> of Preparation Example 1, -yl) -9-phenyl-9H-carbazole.

GC-Mass (calculated: 479.16 g / mol, measured: 479 g / mol)

&Lt; Step 2 > IC Synthesis of -18

(2-nitrophenyl) -1H-indole obtained in Step 1 of Preparation Example 16 was used instead of 5- (2-nitrophenyl) -1-phenyl-1H- indole used in Step 4 of Preparation Example 1 4-yl) -indol-1-yl) -9-phenyl-9H-carbazole (7.62 g, 15.91 mmol) .

GC-Mass (calculated: 447.17 g / mol, measured: 447 g / mol)

[ Preparation Example  17] Compound IC -19 Synthesis

<Step 1> Synthesis of 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (5- (2-nitrophenyl) -1 H- indol- synthesis

(2-nitrophenyl) -1H-indole (11 g, 46.17 mmol) was used instead of 5- (2-nitrophenyl) -1H-indole used in Step 3 of Preparation Example 1 and 3-bromo <Step 3> of Preparation Example 1 was repeated except that 4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole (33.03 g, 69.26 mmol) The same procedure was followed to obtain 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (5- (2-nitrophenyl) -1H-indol- &Lt; / RTI >

GC-Mass (calculated: 634.21 g / mol, measured: 634 g / mol)

2-yl) -9H-carbazol-3-yl) -3,10-dihydropyrrolo [3,2-a] Synthesis of carbazole

(4,6-diphenyl-1,3-dioxolan-2-yl) -propan-1-ol obtained in Step 1 of Preparation Example 17 was used in place of 5- (2-nitrophenyl) 1-yl) -9H-carbazole (10.09 g, 15.91 mmol) was used in place of 5-triazin-2-yl) -3- (5- (2- nitrophenyl) 1 < Step 4 >, the compound IC-19 was obtained.

GC-Mass (theory: 602.22 g / mol, measured: 602 g / mol)

[Preparation Example 18] Synthesis of Compound IC-20

<Step 1> 5- bromo -2- phenyl -1H- indole Synthesis of

Pd (OAc) ₂ (1.43 g, 5 mol%), Triphenylphosphine (1.67 g, 5 mol%) was added to a solution of 5-bromo-1H- indole (25 g, 0.13 mol), Iodobenzene (31.22 g, 0.15 mol) , KOAc (37.55 g, 0.38 mol) and H ₂ O (300 ml) were mixed and then stirred at 110 ° C for 24 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5-bromo- (16.66 g, yield 48%).

^{1 H-NMR: δ 6.89 (} dd, 1H), 7.20 (dd, 1H), 7.34 (m, 1H), 7.36 (d, 1H), 7.47 (t, 2H), 7.71 (d, 1H), 7.86 ( dd, 2 H), 11.74 (s, 1 H)

<Step 2> Synthesis of 5- (2- nitrophenyl )-2- phenyl -1H- indole Synthesis of

2-phenyl-1H-indole (15 g, 55.12 mmol) obtained in Step 1 of Preparation Example 18 and NaOH (6.61 g, 165.36 mmol) and THF / H ₂ O (200 ml / 100 ml) were mixed. Then Pd (PPh ₃ ) ₄ (3.18 g, 5 mol) was added at 40 ° C and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto. 2-Nitrophenyl-2-phenyl-1H-indole (10.74 g, yield 62%) was obtained after purification by column chromatography (Hexane: EA = 5: 1 (v / v) &Lt; / RTI &gt;

^{1 H-NMR: δ 6.88 (} dd, 1H), 7.21 (d, 1H), 7.32 (m, 1H), 7.34 (d, 1H), 7.46 (m, 3H), 7.64 (m, 2H), 7.77 ( d, 2H), 8.02 (d, 2H), 11.73 (s, 1H)

&Lt; Step 3 > 5- (2- nitrophenyl ) -1,2- 피덴 -1H- indole Synthesis of

(2-nitrophenyl) -2-phenyl-1H-indole (prepared in Step 2 of Preparation Example 18 instead of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 5- (2-nitrophenyl) -1,2-diphenyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1,

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

&Lt; Step 4 > IC Synthesis of -20

(2-nitrophenyl) -1,2-dimethyl-1H-indole obtained in Step 3 of Preparation Example 18 was used instead of 5- (2-nitrophenyl) The compound IC-20 was obtained in the same manner as in <Step 4> of Preparation Example 1 except that diphenyl-1H-indole (9.34 g, 23.94 mmol) was used.

GC-Mass (358.15 g / mol, measured: 358 g / mol)

[ Preparation Example  19] Compound IC Synthesis of -21

<Step 1> 6- chloro -2- phenyl -1H- indole Synthesis of

Chloro-1H-indole instead of iodobenzene and bromobenzene (23.55 g, 0.13 mol) instead of 5-bromo-1H-indole used in Step 1 of Preparation Example 18 instead of 6-chloro- 6-chloro-2-phenyl-1H-indole was obtained by following the procedure of <Step 1> of Preparation Example 20-18,

^{1 H-NMR: δ 6.92 (} d, 1H), 7.02 (dd, 1H), 7.33 (t, 1H), 7.41 (s, 1H), 7.47 (t, 2H), 7.54 (d, 1H), 7.85 ( d, 2 H), 11.68 (s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl )-2- phenyl -1H- indole Synthesis of

2-phenyl-1H-indole (15 g, 55.12 mmol) obtained in Step 1 of Preparation Example 19 was used instead of 5-bromo-2-phenyl-1H- indole used in Step 2 of Preparation Example 18 (2-nitrophenyl) -2-phenyl-1H-indole was obtained by following the procedure of <Step 2> of Preparation Example 18,

^{1 H-NMR: δ 6.91 (} d, 1H), 7.03 (d, 1H), 7.31 (t, 1H), 7.42 (s, 1H), 7.48 (m, 3H), 7.53 (d, 1H), 7.76 ( m, 3H), 8.01 (d, 2H), 11.66 (s, IH)

&Lt; Step 3 > 6- (2- nitrophenyl ) -1,2- 피덴 -1H- indole Synthesis of

(2-nitrophenyl) -2-phenyl-1H-indole (prepared in Step 2 of Preparation Example 19 instead of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1,2-diphenyl-1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1, except that 10.74 g (34.20 mmol)

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

<Step 4> Synthesis of 6- (2- nitrophenyl ) -1,2- 피덴 -1H- indole Synthesis of

(2-nitrophenyl) -1,2-dimethyl-1H-indole obtained in Step 3 of Preparation Example 19 was used instead of 5- (2-nitrophenyl) The same procedure as in <Step 4> of Preparation Example 1 was conducted except that diphenyl-1H-indole (9.34 g, 23.94 mmol) was used to obtain compound IC-21.

GC-Mass (358.15 g / mol, measured: 358 g / mol)

[Preparation Example 20] Synthesis of Compound IC-22

<Step 1> 6- chloro -3- phenyl -1H- indole Synthesis of

Pd (OAc) ₂ (1.86 g, 5 moles), triphenylphosphine (2.17 g, 5 mol%), bromobenzene (31.19 g, 0.20 mol) K ₂ CO ₃ (68.64 g, 0.50 mol) and 1,4-dioxane (300 ml) were mixed and then stirred at 130 ° C for 18 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 6-chloro-3-phenyl- (24.5 g, yield 65%).

^{1 H-NMR: δ 7.10 (} dd, 1H), 7.25 (m, 1H), 7.43 (t, 2H), 7.49 (d, 1H), 7.67 (dd, 2H), 7.73 (d, 1H), 7.85 ( d, 1 H), 11.49 (s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl ) -3- phenyl -1H- indole Synthesis of

3-phenyl-1H-indole (15 g, 55.12 mmol) obtained in Step 1 of Preparation Example 20 was used instead of 5-bromo-2-phenyl-1H- indole used in Step 2 of Preparation Example 18 2-nitrophenyl) -3-phenyl-1H-indole was obtained by following the procedure of <Step 2> of Preparation Example 20-18,

^{1 H-NMR: δ 7.11 (} d, 1H), 7.26 (m, 1H), 7.44 (t, 2H), 7.48 (m, 2H), 7.55 (m, 3H), 7.61 (d, 1H), 7.73 ( d, 1 H), 8.00 (d, 2H), 11.48 (s, 1 H)

&Lt; Step 3 > 6- (2- nitrophenyl ) -1,3- 피덴 -1H- indole Synthesis of

(2-nitrophenyl) -3-phenyl-1H-indole (prepared in Step 2 of Preparation Example 20 instead of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1,3-diphenyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1, except that the compound (12.11 g, 38.58 mmol)

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

<Step 4> Synthesis of 6- (2- nitrophenyl ) -1,3- 피덴 -1H- indole Synthesis of

(2-nitrophenyl) -1,3-dioxolan-2-one obtained in Step 3 of Preparation Example 20 was used instead of 5- (2-nitrophenyl) The same procedure as in <Step 4> of Preparation Example 1 was conducted except that diphenyl-1H-indole (10.53 g, 27.00 mmol) was used to obtain compound IC-22.

GC-Mass (358.15 g / mol, measured: 358 g / mol)

[Preparation Example 21] Synthesis of Compound IC-23

<Step 1> 5- bromo -2,3- 피덴 -1H- indole Synthesis of

Except that 5-bromo-2-phenyl-1H-indole (46.24 g, 0.17 mol) was used instead of 6-chloro-1H-indole used in <Step 1> of Preparation Example 20, 5-bromo-2,3-diphenyl-1H-indole was obtained in the same manner as in <Step 1>.

^{1 H-NMR: δ 7.23 (} d, 1H), 7.31 (t, 2H), 7.43 (m, 6H), 7.67 (d, 1H), 7.71 (d, 1H), 7.84 (d, 2H), 11.34 ( s, 1 H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) -2,3- 피덴 -1H- indole Synthesis of

Bromo-2,3-diphenyl-1H-indole (35.40 g, obtained in Step 1 of Preparation Example 21) obtained in Step 2 of Preparation Example 18 was used instead of 5-bromo-2-phenyl- , 0.102 mol) was used in place of 2-pyrrolidone to obtain 5- (2-nitrophenyl) -2,3-diphenyl-1H-indole.

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

&Lt; Step 3 > 5- (2- nitrophenyl ) -2,3- 피덴 -1H- indole Synthesis of

(2-nitrophenyl) -2,3-diphenyl-1H-indole obtained in Step 2 of Preparation Example 21 was used instead of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1, (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1, except that indole (27.84 g, 71.40 mmol) .

GC-Mass (calculated: 466.17 g / mol, measured: 466 g / mol)

&Lt; Step 4 > IC Synthesis of -23

(2-nitrophenyl) -1,2,3-thiadiazole obtained in Step 3 of Preparation Example 21 instead of 5- (2-nitrophenyl) -1-phenyl-1H- indole used in Step 4 of Preparation Example 1, Compound IC-23 was obtained by following the procedure of <Step 4> of Preparation Example 1, except that 3-triphenyl-1H-indole (19.96 g, 42.84 mmol) was used.

GC-Mass (calculated: 434.18 g / mol, measured: 434 g / mol)

[Preparation Example 22] Synthesis of compound IC-24

<Step 1> 6- chloro -2,3- 피덴 -1H- indole Synthesis of

Except that 6-chloro-2-phenyl-1H-indole (34.05 g, 0.15 mmol) was used instead of 6-chloro-1H-indole used in <Step 1> of Preparation Example 20, 6-chloro-2,3-diphenyl-1H-indole was obtained in the same manner as in <Step 1>.

^{1 H-NMR: δ 7.18 (} d, 1H), 7.29 (t, 2H), 7.50 (m, 6H), 7.62 (d, 1H), 7.75 (d, 1H), 7.89 (d, 2H), 11.35 ( s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl ) -2,3- 피덴 -1H- indole Synthesis of

2,3-diphenyl-1H-indole (27.27 g, obtained in Step 1 of Preparation Example 22) was used instead of 5-bromo-2-phenyl-1H- indole used in Step 2 of Preparation Example 18 2-nitrophenyl) -2,3-diphenyl-1H-indole was obtained by following the procedure of <Step 2> of Preparation Example 18,

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

&Lt; Step 3 > 6- (2- nitrophenyl ) -1,2,3- 트리 피닐 -1H- indole Synthesis of

(2-nitrophenyl) -2,3-diphenyl-1H-indole obtained in Step 2 of Preparation Example 22 was used in place of 5- (2-nitrophenyl) -1H- indole used in Step 3 of Preparation Example 1, (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1 except that indole (11.70 g, 30.00 mmol) .

GC-Mass (calculated: 466.17 g / mol, measured: 466 g / mol)

&Lt; Step 4 > IC Synthesis of -24

(2-nitrophenyl) -1,2,3-thiadiazole obtained in Step 3 of Preparation Example 22 was used instead of 5- (2-nitrophenyl) -1-phenyl-1H- indole used in Step 4 of Preparation Example 1, The same procedure as in <Step 4> of Preparation Example 1 was carried out except that 3-triphenyl-1H-indole (9.78 g, 21.00 mmol) was used to obtain compound IC-24.

GC-Mass (calculated: 434.18 g / mol, measured: 434 g / mol)

[Preparation Example 23] Synthesis of Compound IC-25

Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole

(10 g, 41.97 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (17.32 g, 50.37 mmol) in a nitrogen atmosphere. , P (t-bu) ₃ (0.85 g, 4.19 mmol) and Toluene (100 ml) were added to a solution of Pd (OAc) ₂ (0.47 g, 5 mol%), NaO After mixing, the mixture was stirred at 110 DEG C for 12 hours.

Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give 1- (3- (4,6-diphenyl -1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole (15.8 g, yield 69%).

GC-Mass (calculated: 545.19 g / mol, measured: 545 g / mol)

&Lt; Step 2 > IC Synthesis of -25

(3- (4,6-diphenyl-1-phenyl-1H-indole) -acetate obtained in Step 1 of Preparation Example 23 was used in place of 5- (2-nitrophenyl) Step 4 of Preparation Example 1 was repeated except that 1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H- indole (15.8 g, 29.00 mmol) The compound IC-25 was obtained.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[Preparation Example 24] Synthesis of compound IC-26

<Step 1> Synthesis of 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole

Instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine used in Step 1 of Preparation Example 23, 17.27 g , 50.37 mmol) was used in place of 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -6- 2-nitrophenyl) -1H-indole.

GC-Mass (calculated: 544.19 g / mol, measured: 544 g / mol)

&Lt; Step 2 > IC Synthesis of -26

(3- (4,6-diphenylpyrimidin-2-yl) -1H-indole obtained in Step 1 of Preparation Example 24 was used instead of 5- (2-nitrophenyl) Step 4 of Preparation Example 1 was carried out, except that the compound IC (1) was used instead of the compound IC (2-yl) phenyl-6- (2-nitrophenyl) -26 < / RTI >

GC-Mass (calculated: 512.20 g / mol, measured: 512 g / mol)

[Preparation Example 25] Synthesis of Compound IC-27

Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitrophenyl) -1H-indole

Except that 5- (2-nitrophenyl) -1H-indole (10 g, 41.97 mmol) was used instead of 6- (2-nitrophenyl) -1H-indole used in Step 1 of Preparation Example 23 (4-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitro phenyl) - 1H-indole.

GC-Mass (calculated: 545.19 g / mol, measured: 545 g / mol)

&Lt; Step 2 > IC -27

11- (3- (4,6-diphenyl-1-phenyl-1H-indole) -acetate obtained in Step 1 of Preparation Example 25 was used in place of 5- (2-nitrophenyl) Step 4 of Preparation Example 1 was repeated except that 1,3,5-triazin-2-yl) phenyl) -5- (2-nitro phenyl) -1H- indole (15.8 g, 29.00 mmol) Gt; IC-27 < / RTI > was obtained.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[Preparation Example 26] Synthesis of compound IC-28

<Step 1> Synthesis of 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -5- (2-nitrophenyl) -1H-indole

1H-indole (10 g, 41.97 mmol) was used instead of 6- (2-nitrophenyl) -1H-indole used in Step 1 of Preparation Example 23 to obtain 2- (3- except that 2- (3-chloro phenyl) -4,6-diphenylpyrimidine (17.27 g, 50.37 mmol) was used in place of chlorophenyl) -4,6-diphenyl-1,3,5- (4-diphenylpyrimidin-2-yl) phenyl) -5- (2-nitrophenyl) -1H-indole.

GC-Mass (calculated: 544.19 g / mol, measured: 544 g / mol)

&Lt; Step 2 > IC -28 Synthesis

(3- (4,6-diphenylpyrimidin-2-yl) phenyl] -1H-indole obtained in Step 1 of Preparation Example 26 was used in place of 5- (2-nitrophenyl) The same procedure as in <Step 4> of Preparation Example 1 was carried out except that 15.7 g (29.00 mmol) of 2-chloropyridin-2-yl) -28.

GC-Mass (calculated: 512.20 g / mol, measured: 512 g / mol)

[Preparation Example 27] Synthesis of Compound IC-29

<Step 1> 9- phenyl -9H- carbazole -2- amine Synthesis of

9.26 g (30.0 mmol) of 2-bromo-9-phenyl-9H-carbazole was dissolved in 100 ml of toluene under a nitrogen stream and then 10.2 ml (150 mmol) of 28% aqueous ammonia and 0.10 g And the mixture was stirred at 110 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent from the filtered organic layer, 6.5 g (yield: 83%) of 9-phenyl-9H-carbazol-2-amine was obtained by column chromatography.

^{1 H-NMR: δ 6.51 (} s, 2H), 6.72 (m, 2H), 7.53 (m, 2H), 7.55 (m, 5H), 7.98 (d, 1H), 8.05 (d, 1H), 8.62 ( d, 1 H)

&Lt; Step 2 > IC Synthesis of -29

Phenyl-9H-carbazol-2-amine was dissolved in H ₂ O / dioxane (10 ml / 90 ml) under nitrogen flow, and then 0.372 g (2 mmol) of triethanolammonium chloride, into the <sub>`H 2 O 0.052 g (0.2</sub> mmol) and <sub>PPh 3 0.158 g (0.6 mmol)</sub> , SnCl 2` 2H 2 O 0.452 g (2 mmol) and stirred at 180 ℃ for 20 hours.

After completion of the reaction, the reaction mixture was poured into aqueous 5% HCl, extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent from the filtered organic layer, 2.8 g of compound IC-29 (yield: 54%) was obtained by column chromatography.

^{1 H-NMR: δ 6.48 (} d, 1H), 7.35 (m, 4H), 7.58 (m, 5H), 7.98 (d, 1H), 8.15 (d, 1H), 8.59 (d, 1H), 10.12 ( s, 1 H)

[Preparation Example 28] Synthesis of compound IC-30

<Step 1> 9- phenyl -9H- carbazole -One- amine Synthesis of

Except that 9.66 g (30.0 mmol) of 1-bromo-9-phenyl-9H-carbazole was used in place of 2-bromo-9-phenyl-9H-carbazole used in Step 1 of Preparation Example 27 (Yield: 80%) of 9-phenyl-9H-carbazol-1-amine was obtained in the same manner as in <Step 1>

^{1 H-NMR: δ 6.37 (} s, 2H), 6.82 (d, 1H), 7.15 (t, 1H), 7.36 (m, 2H), 7.62 (m, 5H), 8.02 (d, 1H), 8.63 ( d, 1 H)

&Lt; Step 2 > IC Synthesis of -30

Phenyl-9H-carbazol-1-amine (5.16 g, 20.0 mmol) obtained in Step 1 of Preparation Example 28 was used instead of 9-phenyl-9H-carbazol-2-amine used in Step 2 of Preparation Example 27, , 2.4 g (yield: 42%) of the compound IC-30 was obtained by carrying out the same procedure as in <Step 2> of Preparation Example 27.

^{1 H-NMR: δ 6.52 (} d, 1H), 7.41 (m, 3H), 7.58 (m, 5H), 8.01 (d, 1H), 8.18 (d, 1H), 8.62 (d, 1H), 10.22 ( s, 1 H)

[Preparation Example 29] Synthesis of Compound IC-31

Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole

(10 g, 41.97 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (17.32 g, 50.37 mmol) in a nitrogen atmosphere. , P (t-bu) ₃ (0.85 g, 4.19 mmol) and Toluene (100 ml) were added to a solution of Pd (OAc) ₂ (0.47 g, 5 mol%), NaO After mixing, the mixture was stirred at 110 DEG C for 12 hours.

Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give 1- (3- (4,6-diphenyl -1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole (15.8 g, yield 69%).

GC-Mass (calculated: 545.19 g / mol, measured: 545 g / mol)

&Lt; Step 2 > IC Synthesis of -31

(3- (4,6-diphenyl-1-phenyl-1H-indole) -acetate obtained in Step 1 of Preparation Example 29 was used in place of 5- (2-nitrophenyl) Step 4 of Preparation Example 1 was repeated except that 1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H- indole (15.8 g, 29.00 mmol) The compound IC-31 was obtained.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

 [Preparation Example 30] Synthesis of compound IC-32

Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitrophenyl) -1H-indole

Except that 5- (2-nitrophenyl) -1H-indole (10 g, 41.97 mmol) was used instead of 6- (2-nitrophenyl) -1H-indole used in Step 1 of Preparation Example 29 (4-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitro phenyl) - 1H-indole.

GC-Mass (calculated: 545.19 g / mol, measured: 545 g / mol)

&Lt; Step 2 > IC -32 synthesis

(3- (4,6-diphenyl-1-phenyl-1H-indole) -acetate obtained in Step 1 of Preparation Example 30 was used in place of 5- (2-nitrophenyl) Step 4 of Preparation Example 1 was repeated except that 1,3,5-triazin-2-yl) phenyl) -5- (2-nitro phenyl) -1H- indole (15.8 g, 29.00 mmol) Gt; IC-32 < / RTI > was obtained.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[ Synthetic example  1] Compound Inv Synthesis of -1

(3 g, 10.63 mmol), 4,4'-dibromo-1,1'-biphenyl (1.33 g, 4.25 mmol) and Cu powder (0.07 g, 1.06 mmol) prepared in Preparation Example 1 under nitrogen stream, , K ₂ CO ₃ (1.47 g, 10.63 mmol), Na ₂ SO ₄ (1.51 g, 10.63 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C for 24 hours.

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain Compound Inv-1 (2 g, yield: 66%).

GC-Mass (calculated: 714.85 g / mol, measured: 715 g / mol)

[ Synthetic example  2] Compound Inv Synthesis of -2

The same procedure as in Synthesis Example 1 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-2 1.64 g, yield: 54%).

GC-Mass (calculated: 714.85 g / mol, measured: 715 g / mol)

[ Synthetic example  3] Compound Inv Synthesis of -3

Except that the compound IC-6 (3 g, 10.63 mmol) obtained in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 1, and the compound Inv-3 ( 1.82 g, yield: 60%).

GC-Mass (calculated: 714.85 g / mol, measured: 715 g / mol)

[ Synthetic example  4] Compound Inv Synthesis of -4

Except that the compound IC-5 (3 g, 10.63 mmol) obtained in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-4 ( 1.52 g, yield: 50%).

GC-Mass (calculated: 714.85 g / mol, measured: 715 g / mol)

[Synthesis Example 5] Synthesis of Compound Inv-5

The procedure of Synthesis Example 1 was repeated except that the compound IC-2 (3 g, 10.63 mmol) obtained in Preparation Example 1 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-4 ( 1.34 g, yield: 44%).

GC-Mass (calculated: 714.85 g / mol, measured: 715 g / mol)

[Synthesis Example 6] Synthesis of compound Inv-6

Except that the compound IC-4 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-6 ( 1.4 g, yield: 46%).

GC-Mass (calculated: 714.85 g / mol, measured: 715 g / mol)

[Synthesis Example 7] Synthesis of compound Inv-7

Except that 2,7-dibromo-9-phenyl-9H-carbazole (1.70 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1, The procedure of Example 1 was repeated to obtain the compound Inv-7 (1.67 g, yield: 53%).

GC-Mass (theory: 803.95 g / mol, measurement: 803 g / mol)

[Synthesis Example 8] Synthesis of Compound Inv-8

Except that 2,7-dibromo-9,9-dimethyl-9H-fluorene (1.50 g, 4.25 mmol) was used in place of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1, The procedure of Synthesis Example 1 was repeated to obtain Compound Inv-8 (1.47 g, yield: 46%).

GC-Mass (calculated: 754.92 g / mol, measured: 754 g / mol)

[Synthesis Example 9] Synthesis of Compound Inv-9

Except that 2,7-dibromo-9,9-diphenyl-9H-fluorene (2.02 g, 4.25 mmol) was used in place of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1, The same procedure as in Synthesis Example 1 was carried out to obtain a compound Inv-9 (1.83 g, yield: 49%).

GC-Mass (theory: 879.06 g / mol, measurement: 879 g / mol)

[Synthesis Example 10] Synthesis of Compound Inv-10

Except that 2,7-dibromo-9,9'-spirobi [fluorene] (2.01 g, 4.25 mmol) was used in place of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1, The procedure of Synthesis Example 1 was repeated to obtain Compound Inv-10 (1.75 g, yield: 47%).

GC-Mass (calculated: 877.04 g / mol, measured: 877 g / mol)

[Synthesis Example 11] Synthesis of Compound Inv-11

4,4'-dibromo-2,2'-dimethyl-1,1'-biphenyl (1.44 g, 4.25 mmol) was used instead of the 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1 The procedure of Synthesis Example 1 was repeated to obtain Compound Inv-11 (1.74 g, yield: 55%).

GC-Mass (742.91 g / mol, measured: 742 g / mol)

[Synthesis Example 12] Synthesis of Compound Inv-12

Except that 3,3'-dibromo-1,1'-biphenyl (1.33 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1, The procedure of Example 1 was followed to obtain the compound Inv-12 (1.85 g, yield: 61%).

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 13] Synthesis of Compound Inv-13

The procedure of Synthesis Example 1 was repeated except that 1,3-dibromobenzene (1.00 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1 Compound Inv-13 (1.90 g, yield: 70%) was obtained.

GC-Mass (theory: 638.76 g / mol, measurement: 638 g / mol)

[Synthesis Example 14] Synthesis of Compound Inv-14

Except that 3,5-dibromo-1,1'-biphenyl (1.33 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1, 1, a compound Inv-14 (1.76 g, yield: 58%) was obtained.

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 15] Synthesis of Compound Inv-15

Except that 2,4-dibromo-6-phenyl-1,3,5-triazine (1.34 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1 Was subjected to the same procedure as in Synthesis Example 1 to obtain Compound Inv-15 (1.34 g, yield: 44%).

GC-Mass (717.82 g / mol, measured: 717 g / mol)

[Synthesis Example 16] Synthesis of compound Inv-16

The same procedure as in Synthesis Example 7 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 7 to obtain the compound Inv-16 1.74 g, yield: 51%).

GC-Mass (theory: 803.95 g / mol, measurement: 803 g / mol)

[Synthesis Example 17] Synthesis of Compound Inv-17

The same procedure as in Synthesis Example 8 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 8 to obtain the compound Inv-17 1.76 g, yield: 55%).

GC-Mass (calculated: 754.92 g / mol, measured: 754 g / mol)

[Synthesis Example 18] Synthesis of Compound Inv-18

The same procedure as in Synthesis Example 9 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 9 to obtain the compound Inv-18 1.76 g, yield: 47%).

GC-Mass (theory: 879.06 g / mol, measurement: 879 g / mol)

[Synthesis Example 19] Synthesis of Compound Inv-19

The same procedure as in Synthesis Example 10 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound Inv-19 ( 1.94 g, yield: 52%).

GC-Mass (calculated: 877.04 g / mol, measured: 877 g / mol)

[Synthesis Example 20] Synthesis of Compound Inv-20

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound Inv-20 1.67 g, yield: 53%).

GC-Mass (742.91 g / mol, measured: 742 g / mol)

[Synthesis Example 21] Synthesis of Compound Inv-21

The procedure of Synthesis Example 12 was repeated except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain Compound Inv-21 2.07 g, yield: 68%).

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 22] Synthesis of compound Inv-22

Except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 13, and the compound Inv-22 ( 1.36 g, yield: 50%).

GC-Mass (theory: 638.76 g / mol, measurement: 638 g / mol)

[Synthesis Example 23] Synthesis of compound Inv-23

The same procedure as in Synthesis Example 14 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 14 to obtain the compound Inv-23 1.73 g, yield: 57%).

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[ Synthetic example  24] Compound Inv Synthesis of -24

The same procedure as in Synthesis Example 15 was carried out except that the compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 15 to obtain the compound Inv-24 1.22 g, yield: 40%).

GC-Mass (717.82 g / mol, measured: 717 g / mol)

[Synthesis Example 25] Synthesis of Compound Inv-25

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-6 (3 g, 10.63 mmol) obtained in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound Inv-25 1.55 g, yield: 49%).

GC-Mass (742.91 g / mol, measured: 742 g / mol)

[Synthesis Example 26] Synthesis of compound Inv-26

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-5 (3 g, 10.63 mmol) obtained in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound Inv-26 1.58 g, yield: 50%).

GC-Mass (742.91 g / mol, measured: 742 g / mol)

[Synthesis Example 27] Synthesis of compound Inv-27

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-2 (3 g, 10.63 mmol) obtained in Preparation Example 1 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound Inv-27 1.95 g, yield: 62%).

GC-Mass (742.91 g / mol, measured: 742 g / mol)

[Synthesis Example 28] Synthesis of compound Inv-28

The procedure of Synthesis Example 11 was repeated except that the compound IC-4 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound Inv-28 1.90 g, yield: 60%).

GC-Mass (742.91 g / mol, measured: 742 g / mol)

[Synthesis Example 29] Synthesis of Compound Inv-29

The same procedure as in Synthesis Example 15 was carried out except that the compound IC-6 (3 g, 10.63 mmol) obtained in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 15 to obtain the compound Inv-29 1.71 g, yield: 56%).

GC-Mass (717.82 g / mol, measured: 717 g / mol)

[Synthesis Example 30] Synthesis of Compound Inv-30

The same procedure as in Synthesis Example 15 was carried out except that the compound IC-5 (3 g, 10.63 mmol) obtained in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 15 to obtain the compound Inv-30 1.92 g, yield: 63%).

GC-Mass (717.82 g / mol, measured: 717 g / mol)

[Synthesis Example 31] Synthesis of Compound Inv-31

The same procedure as in Synthesis Example 15 was carried out except that the compound IC-2 (3 g, 10.63 mmol) obtained in Preparation Example 1 was used instead of the compound IC-1 used in Synthesis Example 15 to obtain the compound Inv-31 1.86 g, yield: 61%).

GC-Mass (717.82 g / mol, measured: 717 g / mol)

[Synthesis Example 32] Synthesis of Compound Inv-32

The procedure of Synthesis Example 15 was repeated except that the compound IC-4 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 15 to obtain the compound Inv-32 1.47 g, yield: 48%).

GC-Mass (717.82 g / mol, measured: 717 g / mol)

[Synthesis Example 33] Synthesis of Compound Inv-33

The same procedure as in Synthesis Example 1 was carried out except that the compound IC-19 (6.40 g, 10.63 mmol) obtained in Preparation Example 17 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-33 ( 2.30 g, yield: 40%).

GC-Mass (calculated: 1355.55 g / mol, measured: 1355 g / mol)

[Synthesis Example 34] Synthesis of compound Inv-34

The same procedure as in Synthesis Example 1 was carried out except that the compound IC-11 (4.61 g, 10.63 mmol) obtained in Preparation Example 9 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-34 2.47 g, yield: 57%).

GC-Mass (theory: 1019.24 g / mol, measurement: 1018 g / mol)

[Synthesis Example 35] Synthesis of compound Inv-35

The same procedure as in Synthesis Example 1 was carried out except that the compound IC-18 (4.75 g, 10.63 mmol) obtained in Preparation Example 16 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-35 2.40 g, yield: 54%).

GC-Mass (calculated: 1045.23 g / mol, measured: 1044 g / mol)

[ Synthetic example  36] Compound Inv Synthesis of -36

The same procedure as in Synthesis Example 1 was carried out except that the compound IC-32 (5.45 g, 10.63 mmol) obtained in Preparation Example 30 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-36 3.25 g, yield: 65%).

GC-Mass (calculated: 1177.36 g / mol, measured: 1177 g / mol)

[Synthesis Example 37] Synthesis of Compound Inv-37

Except that Compound IC-10 (3.80 g, 10.63 mmol) obtained in Preparation Example 8 was used instead of Compound IC-1 used in Synthesis Example 1 to obtain Compound Inv-37 ( 2.28 g, yield: 62%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 38] Synthesis of Compound Inv-38

Except that the compound IC-13 (3.80 g, 10.63 mmol) obtained in Preparation Example 11 was used instead of the compound IC-1 used in Synthesis Example 1, and the compound Inv-38 ( 2.14 g, yield: 58%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 39] Synthesis of Compound Inv-39

<Step 1> Synthesis of 3,7-diphenyl-3,10-dihydropyrrolo [3,2-a] carbazole

Compound 7-bromo-3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (5 g, 13.84 mmol) obtained in Preparation Example 5 and phenylboronic acid (2.03 g, 16.61 mmol), NaOH (1.66 g, 41.52 mmol) and _{THF / H 2 O (100 ml} / 500 ml) , and then, place the _{Pd (PPh 3) 4 (0.80} g, 5 mol%) in 40 ℃, 80 mixing Lt; 0 &gt; C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 3,7-diphenyl-3,10-dihydropyrrolo [3,2-a] carbazole.

<Step 2> Synthesis of compound Inv-39

3,7-diphenyl-3,10-dihydropyrrolo [3,2-a] carbazole (3.80 g, 10.63 mmol) obtained in Step 1 of Synthesis Example 39 was used instead of Compound IC- The procedure of Synthesis Example 1 was repeated to obtain a compound Inv-39 (1.47 g, yield: 40%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 40] Synthesis of compound Inv-40

Except that the compound IC-20 (3.80 g, 10.63 mmol) obtained in Preparation Example 18 was used instead of the compound IC-1 used in Synthesis Example 1, and the compound Inv-40 ( 2.62 g, yield: 71%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 41] Synthesis of Inv-41

Except that the compound IC-16 (4.61 g, 10.63 mmol) obtained in Preparation Example 16 was used instead of the compound IC-1 used in Synthesis Example 1, and the compound Inv-41 ( 1.77 g, yield: 41%).

GC-Mass (theory: 1019.24 g / mol, measurement: 1019 g / mol)

[Synthesis Example 42] Synthesis of Compound Inv-42

Except that the compound IC-17 (5.45 g, 10.63 mmol) obtained in Preparation Example 15 was used instead of the compound IC-1 used in Synthesis Example 1, and the compound Inv-42 ( 3.00 g, yield: 60%).

GC-Mass (calculated: 1177.36 g / mol, measured: 1177 g / mol)

[Synthesis Example 43] Synthesis of compound Inv-43

The procedure of Synthesis Example 1 was repeated except that the compound IC-15 (3.80 g, 10.63 mmol) obtained in Preparation Example 13 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-43 ( 1.44 g, yield: 39%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 44] Synthesis of Compound Inv-44

The procedure of Synthesis Example 1 was repeated except that the compound IC-14 (3.80 g, 10.63 mmol) obtained in Preparation Example 12 was used instead of the compound IC-1 used in Synthesis Example 39 to obtain the compound Inv-44 2.54 g, yield: 69%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 45] Synthesis of Compound Inv-45

The procedure of Synthesis Example 39 was repeated except that the compound IC-8 (3.80 g, 10.63 mmol) obtained in Preparation Example 6 was used instead of the compound IC-7 used in Step 1 of Synthesis Example 39 to obtain Compound Inv -45 (1.80 g, yield: 49%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 46] Synthesis of compound Inv-46

Except that the compound IC-21 (3.80 g, 10.63 mmol) obtained in Preparation Example 19 was used instead of the compound IC-1 used in Synthesis Example 1, and the compound Inv-46 ( 1.88 g, yield: 51%).

GC-Mass (calculated: 867.05 g / mol, measured: 867 g / mol)

[Synthesis Example 47] Synthesis of compound Inv-47

The same procedure as in Synthesis Example 1 was carried out except that the compound IC-29 (3.00 g, 10.63 mmol) obtained in Preparation Example 27 was used instead of the compound IC-1 used in Synthesis Example 1 to obtain the compound Inv-47 1.88 g, yield: 62%).

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 48] Synthesis of Compound Inv-48

Except that the compound IC-30 (3.00 g, 10.63 mmol) obtained in Preparation Example 28 was used in place of the compound IC-1 used in Synthesis Example 1, and the compound Inv-48 ( 1.67 g, yield: 58%).

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 49] Synthesis of compound Inv-49

Synthesis of 10- (4'-bromo- [1,1'-biphenyl] -4-yl) -3-phenyl-3,10-dihydropyrrolo [3,2-a]

(1.2 g, 4.25 mmol), 4,4'-dibromo-1,1'-biphenyl (1.33 g, 4.25 mmol) and Cu powder (0.03 g, 0.43 mmol) obtained in Preparation Example 1 under a nitrogen stream. , K ₂ CO ₃ (0.59 g, 0.43 mmol), Na ₂ SO ₄ (0.6 g, 0.43 mmol) and nitrobenzene (50 ml) were mixed and stirred at 210 ° C. for 24 hours.

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain 10- (4'-bromo- [1,1'- ) -3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole.

&Lt; Step 2 > Inv Synthesis of -49

9H-carbazole (0.71 g, 4.25 mmol) was used instead of the compound IC-1 used in Synthesis Example 1, and the compound obtained in Step 1 of Synthesis Example 49 instead of 4,4'-dibromo-1,1'- 3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (2.18 g, 4.25 mmol) was used instead of 10- , The compound Inv-49 (0.74 g, yield: 29%) was obtained in the same manner as in Synthesis Example 1.

GC-Mass (calculated: 599.72 g / mol, measured: 599 g / mol)

[ Synthetic example  50] Compound Inv Synthesis of -50

The procedure of Synthesis Example 49 was repeated except that the compound IC-6 (1.2 g, 4.25 mmol) obtained in Preparation Example 4 was used instead of the compound IC-1 used in Step 1 of Synthesis Example 49 Compound Inv-50 (0.59 g, yield: 23%) was obtained.

GC-Mass (calculated: 599.72 g / mol, measured: 599 g / mol)

 [Synthesis Example 51] Synthesis of Compound Inv-51

The procedure of Synthetic Example 49 was repeated except that the compound IC-6 (1.2 g, 4.25 mmol) obtained in Preparation Example 4 was used instead of 9H-carbazole used in Step 2 of Synthesis Example 49 to obtain the compound Inv-51 (0.40 g, yield: 13%).

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 52] Synthesis of compound Inv-52

Synthesis of 7- (9H-carbazol-9-yl) phenyl) -3-phenyl-3,10-dihydropyrrolo [3,2-a]

9H-carbazol-9-yl) phenyl) boronic acid (4.78 g, 16.61 mmol) and NaOH (1.66 g, 41.52 mmol) were added to a solution of compound IC- mmol) and insert the a mixture of _{THF / H 2 O (100 ml} / 500 ml) and then, at _{40 ℃ Pd (PPh 3) 4} (0.80 g, 5 mol%), and the mixture was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto, followed by filtration to obtain an organic layer. The solvent was removed from the obtained organic layer and then the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 7- (9H-carbazol- , 10-dihydropyrrolo [3,2-a] carbazole.

<Step 2> Synthesis of compound Inv-52

Phenyl) -3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (2.23 g) obtained in Step 1 of Synthesis Example 52 g, 4.25 mmol), iodobenzene (2.17 g, 10.63 mmol), Cu powder (0.07 g, 1.06 mmol), K ₂ CO ₃ (1.47 g, 10.63 mmol), Na ₂ SO ₄ And nitrobenzene (100 ml), followed by stirring at 210 ° C for 24 hours.

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride. Then, water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain Compound Inv-52 (1.10 g, yield: 43%).

GC-Mass (calculated: 599.72 g / mol, measured: 599 g / mol)

[Synthesis Example 53] Synthesis of compound Inv-53

The procedure of Synthetic Example 52 was repeated except that the compound IC-6 (1.2 g, 4.25 mmol) obtained in Preparation Example 4 was used instead of the compound IC-1 used in Step 1 of Synthesis Example 52 Compound Inv-53 (1.02 g, yield: 40%) was obtained.

GC-Mass (calculated: 599.72 g / mol, measured: 599 g / mol)

[Synthesis Example 54] Synthesis of compound Inv-54

Except that 2,5-bis (4-bromophenyl) -1,3,4-oxadiazole (1.62 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1 , The procedure of Synthesis Example 1 was repeated to obtain the compound Inv-54 (1.83 g, yield: 55%).

GC-Mass (theory: 782.89 g / mol, measured: 782 g / mol)

[Synthesis Example 55] Synthesis of compound Inv-55

Instead of 4,4'-dibromo-1,1'-biphenyl, compound IC-6 (3 g, 10.63 mmol) obtained in Preparation Example 4 was used instead of compound IC-1 used in Synthesis Example 1, (1.76 g, yield: 53%) was obtained by following the same procedure as in Synthesis Example 54 1, except that 4-bromophenyl-1,3,4-oxadiazole (1.62 g, 4.25 mmol) %).

GC-Mass (theory: 782.89 g / mol, measured: 782 g / mol)

[Synthesis Example 56] Synthesis of Compound Inv-56

Except that 2,5-bis (4-bromophenyl) -1,3,4-thiadiazole (1.68 g, 4.25 mmol) was used instead of 4,4'-dibromo-1,1'-biphenyl used in Synthesis Example 1 , The same procedure as in Synthesis Example 1 was carried out to obtain Compound Inv-56 (1.70 g, yield: 50%).

GC-Mass (theory: 798.95 g / mol, measurement: 799 g / mol)

[Synthesis Example 57] Synthesis of compound Inv-57

Instead of 4'-dibromo-1,1'-biphenyl, compound IC-6 (3 g, 10.63 mmol) obtained in Preparation Example 4 was used instead of compound IC-1 used in Synthesis Example 1, (1.63 g, yield: 48%) was obtained by carrying out the same procedure as in Synthesis Example 56 1, except that 1-bromophenyl-1,3,4-thiadiazole (1.68 g, 4.25 mmol) .

GC-Mass (theory: 798.95 g / mol, measurement: 799 g / mol)

[Synthesis Example 58] Synthesis of Compound Inv-58

(3 g, 10.63 mmol) and 2- (biphenyl-4-yl) -4,6-dibromo-1,3,5-triazine (1.66 g, 4.25 mmol) , Potassium carbonate powder (0.07 g, 1.06 mmol), K ₂ CO ₃ (1.47 g, 10.63 mmol), Na ₂ SO ₄ (1.51 g, 10.63 mmol) and nitrobenzene (100 ml) Lt; / RTI &gt;

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain Compound Inv-58 (2.06 g, yield: 61%).

GC-Mass (theory: 793.91 g / mol, measured: 793 g / mol)

[Synthesis Example 59] Synthesis of Compound Inv-59

(3,5-dibromophenyl) -4,6-diphenyl-1,3-dibromo-1,3,5-triazine was used in place of the compound 2- (biphenyl- (2.03 g, yield: 55%) was obtained in the same manner as in Synthesis Example 58, except that 5-triazine (1.98 g, 4.25 mmol)

GC-Mass (calculated: 870.01 g / mol, measured: 870 g / mol)

[Synthesis Example 60] Synthesis of Compound Inv-60

(4.31 g, 15.3 mmol), 1,3,5-tribromobenzene (1.33 g, 4.25 mmol), Cu powder (0.10 g, 1.53 mmol) and K ₂ CO ₃ 2.11 g, 15.3 mmol), Na ₂ SO ₄ (2.17 g, 15.3 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C for 24 hours.

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which the water had been removed and then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain Compound Inv-60 (1.76 g, yield: 45%).

GC-Mass (calculated: 922.04 g / mol, measured: 922 g / mol)

[Example 1] Production of organic EL device

The compound Inv-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes , And the substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / Compound Inv-1 + 10% Ir (ppy) ₃ (30 Å nm) / BCP (10 nm) / Alq ₃ (30 nm) on the ITO transparent electrode prepared above. ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used in the device fabrication are as follows.

[Examples 2 to 57] Preparation of organic EL device

Inv-2 to Inv-57 synthesized in Synthesis Examples 2 to 57, respectively, were used instead of the compound Inv-1 used as a host material in the formation of the light-emitting layer in Example 1, Thereby preparing an organic EL device.

[Comparative Example 1] Fabrication of organic EL device

An organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound Inv-1 used as the luminescent host material in the formation of the light emitting layer in Example 1.

The structure of CBP used is as follows.

[Evaluation Example 1]

The organic EL devices manufactured in Examples 1 to 57 and Comparative Example 1 were measured for driving voltage and current efficiency at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 1 Compound Inv-1 6.68 41.1 Example 2 Compound Inv-2 6.68 41.2 Example 3 Compound Inv-3 6.85 40.9 Example 4 Compound Inv-4 6.83 41.3 Example 5 Compound Inv-5 6.85 39.2 Example 6 Compound Inv-6 6.89 41.7 Example 7 Compound Inv-7 6.91 38.9 Example 8 Compound Inv-8 6.67 40.9 Example 9 Compound Inv-9 6.65 42.1 Example 10 Compound Inv-10 6.63 41.1 Example 11 Compound Inv-11 6.65 39.1 Example 12 Compound Inv-12 6.66 40.3 Example 13 Compound Inv-13 6.7 41.2 Example 14 Compound Inv-14 6.73 39.8 Example 15 Compound Inv-15 6.75 39.3 Example 16 Compound Inv-16 6.88 39.4 Example 17 Compound Inv-17 6.88 38.8 Example 18 Compound Inv-18 6.72 41.3 Example 19 Compound Inv-19 6.69 41.3 Example 20 Compound Inv-20 6.69 38.8 Example 21 Compound Inv-21 6.68 38.9 Example 22 Compound Inv-22 6.65 40.5 Example 23 Compound Inv-23 6.61 40.8 Example 24 Compound Inv-24 6.65 40.3 Example 25 Compound Inv-25 6.65 41.9 Example 26 Compound Inv-26 6.68 40.8 Example 27 Compound Inv-27 6.69 41.8 Example 28 Compound Inv-28 6.73 40.5 Example 29 Compound Inv-29 6.74 41.1 Example 30 Compound Inv-30 6.75 39.5 Example 31 Compound Inv-31 6.83 41.2 Example 32 Compound Inv-32 6.73 42.2 Example 33 Compound Inv-33 6.87 42.8 Example 34 Compound Inv-34 6.91 43.2 Example 35 Compound Inv-35 6.88 39.1 Example 36 Compound Inv-36 6.91 39.4 Example 37 Compound Inv-37 6.69 38.5 Example 38 Compound Inv-38 6.67 41.2 Example 39 Compound Inv-39 6.63 41.3 Example 40 Compound Inv-40 6.61 41.5 Example 41 Compound Inv-41 6.6 39.3 Example 42 Compound Inv-42 6.63 39.1 Example 43 Compound Inv-43 6.62 40.9 Example 44 Compound Inv-44 6.66 41 Example 45 Compound Inv-45 6.68 40.5 Example 46 Compound Inv-46 6.67 39.5 Example 47 Compound Inv-47 6.65 41.3 Example 48 Compound Inv-48 6.74 40.9 Example 49 Compound Inv-49 6.85 41.2 Example 50 Compound Inv-50 6.89 42.6 Example 51 Compound Inv-51 6.83 40.7 Example 52 Compound Inv-52 6.73 41.3 Example 53 Compound Inv-53 6.69 39.1 Example 54 Compound Inv-54 6.67 39.3 Example 55 Compound Inv-55 6.66 40.8 Example 56 Compound Inv-56 6.64 41.2 Example 57 Compound Inv-57 6.66 40.8 Comparative Example 1 CBP 6.93 38.2

As shown in Table 1, green organic EL devices (organic EL devices manufactured in Examples 1 to 57, respectively) using the compounds (Inv-1 to Inv-57) according to the present invention as light emitting layer materials Device) exhibits excellent current efficiency and excellent driving voltage in comparison with the green organic EL device (organic EL device manufactured in Comparative Example 1) using the host material CBP in the related art.

[ Example  58] - Organic EL  Device manufacturing

The compound Inv-15 synthesized in Synthesis Example 15 was subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes , And the substrate was transferred to a vacuum evaporator.

The hole injection layer was formed by thermally vacuum depositing DS-HIL (Doosan) on the prepared ITO (anode) to a thickness of 800 ANGSTROM, and α-NPB ( N , N'- N- di (naphthalene-1-yl) -N , N- diphenylbenzidine) was vacuum-deposited to a thickness of 150 Å to form a hole transport layer.

Thereafter, m-CP (1,3-di (9H-carbazol-9-yl) benzene) was used as a host material and the compound Inv-15 synthesized in Synthesis Example 1 was doped with 6% The hole transport layer was vacuum-deposited on the hole transport layer to form a light emitting layer.

Subsequently, Alq ₃ , which is an electron transporting material, was vacuum deposited on the light emitting layer to a thickness of 250 Å to form an electron transporting layer. Then, LiF as an electron injecting material was deposited on the electron transporting layer to form an electron injecting layer Next, aluminum was vacuum deposited on the electron injecting layer to a thickness of 2000 Å to form a cathode, thereby fabricating an organic electroluminescent device.

The structures of α-NPB and m-CP used are as follows.

[Examples 59 to 66] Preparation of organic EL device

Inv-29, Inv-30, Inv-31, Inv-32, Inv-58, Inv-59 and Inv-60 were used instead of the compound Inv-15 used as a dopant in the formation of the light- Respectively, to prepare an organic electroluminescent device.

[Comparative Example 2] Production of organic EL device

Except that DS-H522 (Doosan) was used in place of m-CP used as a host material in the formation of the light-emitting layer in Example 58 and C-545T was used in place of Compound Inv-15 used as a dopant material. The organic electroluminescent device was fabricated in the same manner as in Example 58.

The structure of C-545T used is as follows.

[Evaluation Example 2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 58 to 66 and Comparative Example 2, respectively, and the results are shown in Table 2 below.

Sample Dopant The driving voltage (V) Current efficiency (cd / A) Example 58 Compound Inv-15 6.1 32.5 Example 59 Compound Inv-24 6.3 31.7 Example 60 Compound Inv-29 6.2 31.9 Example 61 Compound Inv-30 6.0 32.2 Example 62 Compound Inv-31 5.5 32.9 Example 63 Compound Inv-32 5.9 32.3 Example 64 Compound Inv-58 5.8 33.1 Example 65 Compound Inv-59 5.7 33.5 Example 66 Compound Inv-60 5.6 32.0 Comparative Example 2 C-545T 6.8 23.0

(Inv-15, Inv-24, Inv-29, Inv-30, Inv-31, Inv-32, Inv-58, Inv-59, Inv-60) (Organic EL devices manufactured in Examples 58 to 66, respectively) in which the dopant of the light emitting layer (dopant of the light emitting layer) was used as the light emitting layer material (dopant of the light emitting layer) Device) exhibits superior performance in terms of current efficiency and driving voltage.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, and that various changes and modifications may be made without departing from the scope of the invention. It is natural to belong.

Claims (12)

A compound represented by any one of the following formulas (4) to (9):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas 4 to 9,
X ₁ and X ₂ are each independently N (Ar ₁ );
Provided that one of the plurality of R ₄ and Ar ₁ is a substituent represented by the following formula (2)
(2)

In Formula 2,
a is 1 or 2;
L is C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryl-and tri-one (heteroaryl-triyl), - tri-yl (aryl-triyl), or heteroaryl
Provided that when a is 1, L is an arylene group having ₆ to ₆₀ carbon atoms or a heteroarylene group having 5 to 60 nuclear atoms,
when a is 2, L is aryl-triyl, or heteroaryl-triyl;
B is a carbazole group, or a substituent represented by the following general formulas (3a) to (3f), wherein when B is plural, they are the same or different from each other;
[Chemical Formula 3]

(3b)

[Chemical Formula 3c]

(3d)

[Formula 3e]

(3f)

In the above formulas (3a) to (3f)
X ₃ and X ₄ are each independently N (Ar ₆ )
Ar ₆ is a single bond and is connected to L of Formula 2;
R ₁ to R ₈ are the same or different from each other and each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms ;
Ar ₁ and Ar ₆ are the same or different and are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms ;
The C ₆ to C ₆₀ arylene group of L, the heteroarylene group having 5 to 60 nuclear atoms, aryl-triyl, heteroaryl-triyl; A carbazole group of B; Wherein R ₁ to R ₈ of the C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group of; And Ar ₁ and Ar ₆ in the C ₁ ~ C ₄₀ alkyl group, C ₆ ~ to C ₆₀ aryl group, and nuclear atoms groups are heteroaryl of 5 to 60 each independently C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C of ₆₀ aryl group, and the number of nuclear atoms being substituted or unsubstituted or with one or more substituents selected from the group consisting of a heteroaryl group of from 5 to 60, but when the plurality of substituents, they may be the same or different from each other. The compound according to claim 1, wherein L is selected from the group consisting of Substituents C1 to C76.

delete delete delete delete The compound according to claim 1, which is selected from the group consisting of compounds represented by the following formulas (11) to (16).
(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

In the above Formulas 11 to 16,
X ₁ , R ₁ to R ₄ , L, a and B are each as defined in claim 1,
Here, the plural R &lt; ₃ &gt; s are the same as or different from each other, and the plurality of R &lt; ₄ &gt; delete delete 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1, 2, and 7. The organic electroluminescent device according to claim 10, wherein the organic compound layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer. 11. The organic electroluminescent device according to claim 10, wherein the organic compound layer containing the compound is a light emitting layer.